3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one

Details

• Internal ID: 3c1dd6a5-6e40-4a39-88be-36e31cf06b11
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=CC(=CC(=C4C3=O)O)OC)C5=CC=C(C=C5)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H]([C@H](O[C@H]2OC3=C(OC4=CC(=CC(=C4C3=O)O)OC)C5=CC=C(C=C5)O)CO)O)O)O)O)O
• InChI: InChI=1S/C28H32O15/c1-10-18(32)21(35)23(37)27(39-10)43-26-22(36)19(33)16(9-29)41-28(26)42-25-20(34)17-14(31)7-13(38-2)8-15(17)40-24(25)11-3-5-12(30)6-4-11/h3-8,10,16,18-19,21-23,26-33,35-37H,9H2,1-2H3/t10-,16+,18-,19-,21+,22-,23+,26+,27-,28-/m0/s1
• InChI Key: BLZNTUOAYPULPN-XGQCAVDUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₅
• Molecular Weight: 608.50 g/mol
• Exact Mass: 608.17412031 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -1.09
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• CHEMBL2071422

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.9148	91.48%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.7117	71.17%
OATP1B1 inhibitior	+	0.8947	89.47%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8669	86.69%
P-glycoprotein inhibitior	-	0.5856	58.56%
P-glycoprotein substrate	-	0.5077	50.77%
CYP3A4 substrate	+	0.6528	65.28%
CYP2C9 substrate	-	0.8740	87.40%
CYP2D6 substrate	-	0.8547	85.47%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.9258	92.58%
CYP2C19 inhibition	-	0.9329	93.29%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	+	0.7599	75.99%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9142	91.42%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	+	0.5363	53.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4235	42.35%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9108	91.08%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.8389	83.89%
Androgen receptor binding	+	0.6858	68.58%
Thyroid receptor binding	+	0.5251	52.51%
Glucocorticoid receptor binding	+	0.5986	59.86%
Aromatase binding	+	0.5694	56.94%
PPAR gamma	+	0.7419	74.19%
Honey bee toxicity	-	0.7341	73.41%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7522	75.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.53%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.11%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.78%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.47%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.29%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	94.58%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.28%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.93%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.62%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.17%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	91.15%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.01%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.54%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.78%	86.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.83%	95.89%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.73%	95.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.16%	97.09%
CHEMBL4208	P20618	Proteasome component C5	82.97%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.24%	94.45%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.32%	93.10%

Plants that contains it

• Abies alba
• Abies pinsapo subsp. marocana
• Ampelocera edentula
• Angelica acutiloba
• Arnica mollis
• Brassica carinata
• Bryonia alba
• Carpha glomerata
• Croton gratissimus
• Cyanostegia angustifolia
• Dactylorhiza viridis
• Diplopterygium glaucum
• Eucalyptus resinifera
• Euphrasia nana
• Eurycoma harmandiana
• Ixeris japonica
• Lysimachia fordiana
• Orthosiphon aristatus
• Oxytropis falcata
• Pterolobium hexapetalum
• Ranunculus asiaticus
• Remirea maritima
• Sinapis alba
• Solanum lanceolatum
• Viburnum erubescens
• Wikstroemia indica
• Xanthorhiza simplicissima

Cross-Links

• PubChem: 60200223
• NPASS: NPC240306
• LOTUS: LTS0168274
• wikiData: Q104938287